From Law School to Literary Agent with Lilly Ghahremani

Maybe you've thought about it. You love books, you love reading, and somewhere in the back of your mind, you've wondered if there's a way to turn that passion into a career that uses your legal skills without actually practicing law.Lilly Ghahremani knew on day one of law school that it wasn't the right fit. She called her mom from a pay phone and said she'd made a mistake. Her mom convinced her to finish the semester, then the year, then the whole degree. Lilly graduated from UCLA Law in 2002 and stumbled into a job with a small practitioner who worked in publishing. That random job listing became the foundation for a 20-plus year career as a literary agent.See show notes at formerlawyer.com/250

Former litigator David Sazant spent years bouncing between practice areas, convinced that if he just worked hard enough and found the right fit, everything would click into place. He moved from insurance defense to construction and commercial litigation, dealing with persistent imposter syndrome the entire time. But the problem wasn't the type of law he practiced—it was that litigation fundamentally contradicted his core values of authenticity and meaningful connection. In this conversation, David shares the moment he realized he needed to leave law entirely, how a single question from a career coach clarified his path forward, and what it was really like to go back to grad school to become a therapist. He also explains why understanding your values is critical for career satisfaction and how acting against those values can lead to anxiety, depression, and declining self-esteem.See show notes at formerlawyer.com/246

Lawyers love a good assessment. Sarah has learned this running The Collab. There's something appealing about taking a test that promises clear answers about who you are and what you should do next.That appeal is also the problem. When you rely on just one assessment, it's easy to treat the results as the definitive answer. You think, "This is who I am. Now I need to find the career that matches." That kind of tunnel vision is exactly why Sarah uses multiple assessments with clients.Every assessment is a tool. It can be valuable and provide insight. But being useful and being something you should govern your career decisions on are two different things. Using multiple assessments means you can see patterns and themes that are more reliable than any single result.Assessments Sarah Uses:Values in Action (VIA) Chestnut Paes Sullivan (CPS) Enneagram CompassGallup CliftonStrengths Assessment (formerly StrengthsFinder)See show notes at formerlawyer.com/295

When the world feels unstable, the idea of introducing more instability into your life by leaving your job can feel impossible. But waiting for things to stabilize before you address your career unhappiness might mean waiting forever.2025 was a difficult year. If you're already in an overwhelming job, everything else happening in the world makes it even harder to think clearly about your career.But even in difficult years, lawyers leave the legal profession and find work they actually want to do. Even when things are rough, it's still possible.See show notes at formerlawyer.com/294

One of the most common questions lawyers ask when they're thinking about leaving is whether they need a bridge job. It's a fair question, but before Sarah can answer it, she needs to know which type of bridge job you're talking about.Because there are actually two very different kinds.See show notes at formerlawyer.com/239

Sometimes people ask Sarah, "Do all the lawyers you work with end up leaving law?" She gets the sense they think she's trying to convince people to abandon their legal careers, like she's running some kind of exit campaign.Let her be clear. She's not here to convince anyone to leave the law.See show notes at formerlawyer.com/251

Maybe you're thinking about leaving the law, but you aren't quite sure you're ready to start working through the process. You're thinking, "I really think this isn't for me, I definitely want to get out eventually, but maybe not at this exact moment." If that sounds like you, there's something you can do.This is going to be the most unsurprising recommendation, but one of the things that's really important for lawyers who are going through the process of figuring out what they want to do that isn't practicing law is therapy.See show notes at formerlawyer.com/293

When lawyers start thinking about leaving, they focus on the practical steps. What career should I pursue? How do I update my resume? What skills do I need? Those things matter, but Sarah consistently hears from lawyers that they underestimated something else. They didn't realize how much they needed to know they weren't alone.The legal profession can be deeply isolating, especially for people who are unhappy. In a field focused on prestige, lawyers often feel like they have to maintain a professional persona just to be taken seriously. It becomes hard to admit that the work doesn't fit, even to yourself. Lawyers who want out often believe they're the only ones who feel that way. They look around at colleagues who seem fine and wonder what's wrong with them for struggling.In this episode Sarah shares why finding even just one or two other people also going through this process can make leaving the law so much easier. See show notes at formerlawyer.com/292

Most people who are thinking about leaving the law spend a long time in a familiar place. They know their job feels awful, they say it to themselves and to other people, and they imagine how much better things could be somewhere else. But imagining you'd like to leave is not the same thing as deciding that you want to. That shift sounds simple, but it's tied up in identity, prestige, sunk costs, and everything you've been taught about what it means to be successful. It's the first real hurdle for a lot of lawyers, and one that's easy to avoid.See show notes at formerlawyer.com/291

There comes a point where the math you’ve been doing in your head stops adding up. You spent years in school. You passed the bar. You took on the loans. You built the career you were told would make it all worth it. Now you’re tired, anxious, or checked out, but the idea of leaving makes your stomach drop. It feels like walking away means none of it mattered.That’s how the sunk cost trap works. It convinces smart people that the only respectable choice is to stick with a decision that’s hurting them. It tells you that if you bail now, everything you put into becoming a lawyer disappears.If you’re stuck in the “I can’t throw this away” spiral and need help figuring out your next step you need to listen to this. See show notes at formerlawyer.com/249